1. Field of the Invention
This invention relates to tetramines prepared by amination of alkoxylated dialdehyde glycol adducts. The compounds of this invention are useful as curing agents for epoxy resins and in preparing polyurea and polyurethane products and in making RIM elastomers.
2. Prior Art
The amination of long alkoxylated alkyl chains terminated by hydroxyl groups is well known in the art.
U.S. Pat. No. 3,654,370 to E. L. Yeakey teaches the amination of polyoxyalkylene polyols to form the corresponding amines by means of ammonia and hydrogen over a catalyst prepared by the reduction of a mixture of the oxides of nickel, copper and chromium. The amination is carried out at a temperature of 150.degree. to 275.degree. C. and 500 to 5000 psig.
U.S. Pat. No. 4,409,399 to H. E. Swift et al., teaches a catalyst for aminating aliphatic alcohols and aldehydes. The unsupported catalyst comprises (1) copper oxide or copper hydroxide and (2) nickel oxide or nickel hydroxide, and optionally (3) an oxide or hydroxide of a Group IIA metal; e.g., magnesium or barium. The reaction is carried out at a temperature of 150.degree. to 250.degree. C. and 1 to 100 atm with continuous water removal.
U.S. Pat. No. 3,390,184 to P. H. Moss et al., teaches a process for converting a secondary alcohol to a high-molecular weight primary amine by means of a hydrogenation-dehydrogenation catalyst comprising at least one member selected from the group consisting of the metals and oxides of nickel and cobalt, together with copper and a metal oxide selected from the group consisting of chromium oxide, molybdenum oxide, manganese oxide and thorium oxide. The reaction is carried out at a temperature of 225.degree. to 260.degree. C. and pressure of 2000 to 4000 psig, with ammonia as the aminating agent.
U.S. Pat. No. 3,373,204 to R. A. Hales et al., teaches a catalytic process for producing secondary amines from derivatives of phenols, alcohols and amines containing 5 to 40 moles of ethylene oxide and propylene oxide. The catalyst is Raney nickel and ammonia or primary alkylamines as the aminating agent. The reaction is carried out at 200.degree. to 275.degree. C. with the evolution of water. Amines include lauryl amine, hexadecyl amine, octadecyl amine, rosin amine and fatty acid amines.
U.S. Pat. No. 3,347,926 to J. D. Zech teaches a catalytic process for aminating primary and secondary aliphatic alcohols. The catalyst comprises a chromium-promoted Raney nickel. The reaction is carried out at 150.degree. to 275.degree. C. with ammonia, primary amines or secondary amines of 1 to 6 carbon atoms.
U.S. Pat. No. 2,923,696 to K. E. Harwell et al., teaches resinous compositions formed by the reaction of an epoxy resin with a high-boiling amine product. The patent further teaches hydrogenation catalysts employing copper, nickel, cobalt and oxides thereof.
U.S. Pat. No. 4,130,590 to Hobbs et al., teaches the production of long-chain unsaturated amines such as N-(alkadienyl)amines and saturated or hydrated derivatives thereof.
U.S. Pat. No. 3,654,370 to E. Pechhold teaches a process for preparing a polyurethane which is the reaction product of (a) an oligomer formal diol made by coupling segments of copolymers of tetrahydrofuran and an alkylene oxide, such as propylene oxide, with formaldehyde, (b) an organic polyisocyanate and a chain extender as exemplified by ethylene glycol, glycerine, etc.
U.S. Pat. No. 4,691,000 to Andre Collart et al., teaches a process for preparing copolymers containing oxymethylene and 2-fluoromethoxyethylene repeating units formed by copolymerizing trioxane with a derivative of a cyclic ether, such as epifluorohydrin.